If you're leading a company of young, mainly unattached folks and don't have other companies depending on your product, then yes, it's more like a gold rush where you all prosper together and the downside of flying the company into a mountain is 'oh, well, we tried and we learned, let's move on to the next thing.'
It's a different matter if your company is staffed by family breadwinners and you have customers that would have serious deletierious consequences if your firm failed. You don't even need to fail, just go through a rough patch and lay off some the workers you hired and trained, or, fail to deliver a project that negatively affects a customer. These are nerve-wracking for CEOs that aren't made of the stuff that can lead firmly through these situations.
Perhaps the better notion is that startup CEOs that really do react poorly to the 'hard stuff' need a plan to move the burdensome work to a 'professional CEO' and step into Chairman/CTO, or somesuch. Keep the fun, keep the equity, offload the hard stuff.
The fear of letting people down can be crippling. To be brutally honest, there is a type of CEO who simply doesn't feel that as deeply as some people, and they tend to do well in the job, especially when times are good.
In my experience, that type of person is not the same type of person who comes up with an idea and creates something out of nothing. You need some real empathy to find product-market fit; you have to actually care about users and early adopters and by extension investors and employees. But that profile I don't think works at a big company, there is a totally different dynamic.
Hence the stereotype of effective CEOs being sociopaths: their empathy is for the money, not anything--or anyone-- else. They can make a lot of decisions that we would consider difficult, in a completely dispassionate manner, and that's how and why they become good for the job.
It's a different matter if your company is staffed by family breadwinners and you have customers that would have serious deletierious consequences if your firm failed. You don't even need to fail, just go through a rough patch and lay off some the workers you hired and trained, or, fail to deliver a project that negatively affects a customer. These are nerve-wracking for CEOs that aren't made of the stuff that can lead firmly through these situations.
Perhaps the better notion is that startup CEOs that really do react poorly to the 'hard stuff' need a plan to move the burdensome work to a 'professional CEO' and step into Chairman/CTO, or somesuch. Keep the fun, keep the equity, offload the hard stuff.